tert-Butyl acrylate → 1-ethyl-3-(methylaminomethyl)-1H-indole

HRID 1361962Notes

Reaction equation

HRID 1361962 reaction equation
C(OC(C)(C)C)(=O)C=C.C(O[C:18]([N:20]([CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]([CH2:32][CH3:33])[CH:24]=1)C)=O)C1C=CC=CC=1.C(OC(N(CC1C2C(=CC=CC=2)N(CC2C=CC=CC=2)C=1)C)=O)C1C=CC=CC=1>>[CH2:32]([N:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23]([CH2:22][NH:20][CH3:18])=[CH:24]1)[CH3:33]

Participants

4

Reactant 3

HCID 15458tert-Butyl acrylateHCID 221390153-[N-(Benzyloxycarbonyl)-N-methylaminomethyl)-1-benzyl-1H-indoleHCID 221391503-[N-(benzyloxycarbonyl)-N-methylaminomethyl]-1-ethyl-1H-indole

Product 1

HCID 221391011-ethyl-3-(methylaminomethyl)-1H-indoleYield 94.8%

Procedure

According to the procedure of Preparation 17 (c), except substituting 3-[N-(benzyloxycarbonyl)-N-methylaminomethyl]-1-ethyl-1H-indole (0.90 g, 2.80 mmole) for the 3-[N-(benzyloxycarbonyl)-N-methylaminomethyl]-1-benzyl-1H-indole, the title compound (0.50 g, 94%) was prepared as a white solid: MS (ES) n/e 189 (M+H)+.

Sources & evidence

ORD record
ord-81a238ec062943829a44344cf5b488ce
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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